U.S. Pat. No. 4,318,863, issued on Mar. 9, 1982 and assigned to International Flavors & Fragrances, describes substituted tricyclodecane derivatives having the generic formula ##STR3## wherein Y is a moiety having a structure selected from the group consisting of: ##STR4## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that one of R.sub.1 and R.sub.2 is hydrogen and the other of R.sub.1 and R.sub.2 is methyl; wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.3 acyl, C.sub.3 or C.sub.4 alkyl or C.sub.3 or C.sub.4 alkenyl; wherein R.sub.4, R.sub.5 and R.sub.6 represent hydrogen or methyl with the additional proviso that one of R.sub.4, R.sub.5 and R.sub.6 is methyl and the other two of R.sub.4, R.sub.5 and R.sub.6 is hydrogen. Also described are processes for using the above defined compounds for their organoleptic properties.
Among the great variety of tricyclodecane derivatives depicted by the above given formula, the following are worth mentioning: ##STR5## (see Examples I and II of the cited U.S. patent).
Though these compounds of the prior art bear a certain similarity, from the structure point of view, with compounds (I) of the instant invention, they present quite distinct organoleptic properties therefrom.
While the first of the described mixtures possess a fragrance profile characterized by a strong maple aroma with pumpkin-like and slightly spicy undertones, the second one shows a fruity, anisic aroma with a raspberry undertone which on dryout becomes fruity and berry-like (see cited U.S. Pat. No. 4,318,863, columns 16 and 17).
We have discovered that the compounds of the instant invention develop a warm aromatic fragrance with a top note reminiscent of certain spicy ingredients like basil or sage. These fragrance characters are to be found in tagete flowers or marigold. They develop moreover an undertone of earthy and woody type which tends to become dominant in the dry-out.
In actual experience, one could not expect to replace the instant compounds of formula (I) with the prior art ones in a given perfume composition. The distinctiveness of their respective odor properties is such that their use satisfies different needs and achieves dissimilar results.
The invention also relates to a method for modifying, enhancing or improving the odour properties of perfume compositions or perfumed articles, which comprises adding thereto a small but olfactively effective amount of a compound represented by one of the formulae given hereinabove.
The invention finally relates to a perfume composition or a perfumed article which comprises, as olfactively active ingredient, a compound represented by one of the formulae given hereinabove.
In the formulae given hereinabove, the term "lower acyl" is deemed to define an acyl radical containing from 1 to 4 carbon atoms, viz. formyl, acetyl, propionyl, butyryl and isobutyryl.